The Habits of Stylish People

Look Your Best Every Single Day By Embracing These Habits

These characteristics are all built on habit. Brian Tracy said, “Successful people are simply those with successful habits.” I have another version geared towards style: Just replace one word. “Stylish people are simply those with stylish habits.”

Yes, even style is built upon habits — which are easy to learn, even if you have no idea where to start.

In fact, some of the most stylish men in the world have put systems in place to help them. With that in mind, here are 15 habits of stylish people, some of which you can implement immediately, even if you don’t know anything about style.

Have Confidence In Who You Are

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This is the foundation on which style (and life, for that matter) is built.

What message do you want to send to the world? Men who know themselves dress accordingly. Are you a banker? Are you a personal trainer? Maybe you’re in a rock band. You might fall into several categories, meaning you’ll have a different style based on what you want your message to be.

No matter the story, if you appear skeptical about your attire, you’ll come off as “fake” and betray the trust people have in you.

Memorize Your Measurements

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This helps speed up the shopping and alteration process that many men dread. When you’re heading out to make a purchase (or to get an item tailored) you can quickly rattle off the exact sizes you need, which saves precious time.

Another area this helps quite a bit in is the online shopping space. Nowadays, entire wardrobes are purchased online, so if you have your measurements memorized you can speed through and get things done. Keep in mind that it might take some trial and error at first, especially when trying a new brand.

Prepare Outfits The Night Before

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Brainpower is a limited (and precious) resource. There are enough decisions in a day that require a large amount of mental energy, so having outfits laid out the night before allows you to set your mind to cruise control in the morning and not waste any energy (or time) piecing outfits together — just grab and go.

Know Your Proportions

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Men come in all shapes and sizes — some are tall, some are short. All stylish men have learned exactly how clothing works in relation to their proportions, meaning they don’t have to ask if something makes them look taller or shorter. They know their body type and how to dress for it.

Here's a quick example:

To look taller, short men should focus on:

Slim pants (Baggy pants create a shorter look)

Monochrome outfits (For a streamlined silhouette)

Vertical Lines (To look taller)

You can use style to put your best foot forward and help hide anything that might make you a little more self-conscious.

Know The Power of Color

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Color scientifically signals different messages (Ex: Red = Power). This is why leaders and political figures focus on the dark suit and red tie look. You can also use color to guide people’s eyes. What on your body would you like to hide? What would you like to show? Adding color draws attention to that spot.

Example: Want to cover up a slight belly?

Wear a structured suit to build up the shoulders and a red tie with a thick double windsor knot to draw attention up to your face. Add a light blue pocket square for some extra spice. Additionally, avoid a belt because the color of the belt will cause people’s eyes to stop at your midsection, dividing the outfit in half. Suspenders or pants with side adjusters are great alternatives.

The goal of color is to guide people’s eyes effortlessly from feet to face without breaking anywhere to take notice.

Be Intentional About Hygiene

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Grooming is another essential habit to build.

Skin, hair and teeth are not the most popular of subjects to cover when you’re out with the guys for beers. But the pretty lady at the bar will take notice of your trimmed cut and pearly whites over your buddies’ coffee stained dentures.

It’s a subtle but noticeable game changer because it takes effort to maintain. When she notices this, you’re sending the message that you care about your health and overall presentation, which in turn boosts your confidence even more.

Fit Is King

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I get approached by men who are on a tight budget with this question all the time:

“What should I focus on when shopping if I don’t have much money?”

Focus on the fit. A less expensive suit that fits well looks better than an Italian-made billowing tent. But if you have Italian wool that hugs the body like a second skin, then consider it game over. Understand fit, and you’re ahead of 90% of men on the style meter.

Respect The Occasion

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I’ve seen plenty of men refuse to follow a dress code because it “wasn’t their style.” This is a very simple but often overlooked concept. Dressing for the occasion is not about you. It’s about showing respect to the host who invited you.

Don’t show up to weddings in a T-shirt (or a tuxedo, because the groom needs to stand out). Upstaging or downstaging is disrespectful to the hosts who invited you to attend. Dressing for the occasion is a sign of respect, so make it a habit to always follow the dress code at events.

Know Your Tailor By Name

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Think of your tailor like the star player that comes in at the end and wins the game. They don’t just give that role to anyone on the practice squad. He has to have a quality that no one else has, which is the ability to give a clutch performance. Any mistakes, and he would no longer be relied on to win.

That is how your tailor should be. He comes in after you’ve done the shopping and takes your outfit from commonplace to outstanding. There are hundreds of poor tailors out there, so do your homework and find a good one. Once you do, build a relationship with him, because a great tailor will consistently take your style from decent to clutch.

Respecting The Style Of Others

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Unless you want to be the arrogant jerk that offers unsolicited advice, keep your mouth shut. It’s like that guy at the gym that walks around and tries to correct everyone’s form. Sure they may be doing it wrong, but if they want help, let them ask. Style is something that is personal to everyone. They might have a reason for what they’re wearing. Even if they did commit a “style sin,” offer compliments on what they did correctly.

Your presentation will speak to your stylish nature and your character and actions will show that you’re a gentleman who respects others. Chances are, the person will thank you and possibly ask for advice then or at a later date because you were kind.

Know When To Break The Rules

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Rules were made to be broken, and style is no exception. In fact, Italians have a word for it: ”Sprezzatura,” which means elegant carelessness. Men who have mastered the foundations of style can begin to experiment with intentional rule breaking. The ones who do it confidently can own it.

One of the coolest examples I’ve seen of this was with a man who had on an impeccable suit and tie with a crooked tie bar. It played perfectly with his outfit and added some flare that stood out from the crowd.

If you were the unsolicited advice giver (from the previous point), how offended would that man have been if you reached out and straightened his tie bar for him?